N-Fluorobenzenesulfonimide → 3-Fluoro-5-phenyl-benzo[b]thiophene-2-carboxylic acid

HRID 409898Notes

Reaction equation

[C:1]1([C:7]2[CH:18]=[CH:17][C:10]3[S:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:34])(=O)=O)=CC=1>C1COCC1>[F:34][C:13]1[C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:18]=[CH:17][C:10]=2[S:11][C:12]=1[C:14]([OH:16])=[O:15]

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of compound 10d (507 mg, 1.99 mmol) in THF (8 mL) at −70° C. was added n-BuLi (1.6 M in hexane, 2.62 mL, 4.19 mmol). The mixture was stirred at −70° C. for 1 h; then a solution of N-fluorobenzenesulfonimide (817.3 mg, 2.59 mmol) in THF (2 mL) was slowly added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The resulting mixture was partitioned between dilute aqueous HCl and EtOAc. The organic solution was washed with water and brine, dried over Na2SO4, and concentrated. The residue was triturated with CH2Cl2, filtered and the solid dried to give compound 10e (391.9 mg). MS m/z (M+H+) 273.0.

Workup

temperatureto warm to room temperature
stirringwas stirred overnight
customThe resulting mixture was partitioned between dilute aqueous HCl and EtOAc
washThe organic solution was washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was triturated with CH2Cl2
filtrationfiltered
customthe solid dried

Sources & evidence

ORD record: ord-53e967530a104946aaf26fe7aace3a86
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759533B2

Reaction notes

Loading…